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Development of New Synthetic Methods for Biaryl Compounds Using Ring-Closing Metathesis

Research Project

Project/Area Number 22550029
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionChiba University

Principal Investigator

YOSHIDA Kazuhiro  千葉大学, 大学院・理学研究科, 准教授 (60375607)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsメタセシス / 閉環 / グラブス触媒 / 芳香族化合物 / ビアリール化合物 / オレフィンメタセシス / ビアリール / エンインメタセシス / ルテニウム
Research Abstract

Biaryl compounds constitute a class of compounds employed in manyresearch fields. Therefore, the development of flexible synthetic methods for these compounds continuesto be an active area of research. The most common method for the preparation of biaryl compounds isthe transition-metal-catalyzed cross-coupling reaction between aryl halides and aryl metal reagents. Thesuccess of this powerful method, however, essentially depends upon the availability of the two couplingpartners. In this study, we developed a new synthetic approach to biaryl compounds from easilyprepared acyclic building blocks. The direct construction of aromatic rings using theRCEM/RCM/elimination sequence provides unique products without the formation of inseparable regioisomers.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (23 results)

All 2013 2012 2011 2010 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (12 results) Remarks (4 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Synthesis of 4-Vinylindoles Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis2013

    • Author(s)
      Kazushi Hayashi, Kazuhiro Yoshida, and Akira Yanagisawa
    • Journal Title

      J. Org. Chem

      Volume: 78 Issue: 7 Pages: 3464-3469

    • DOI

      10.1021/jo400099x

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Carbocyclic Ring of Indoles Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis Org2011

    • Author(s)
      Kazuhiro Yoshida, Kazushi Hayashi, and Akira Yanagisawa
    • Journal Title

      Lett

      Volume: 13 Issue: 18 Pages: 4762-4765

    • DOI

      10.1021/ol201510u

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ring Size-Selective Ring-Closing Olefin Metathesis: Taking Advantage of the Deleterious Effect of Ethylene Gas Adv2011

    • Author(s)
      Kazuhiro Yoshida, Yuto Kano, Hidetoshi Takahashi, and Akira Yanagisawa
    • Journal Title

      Synth. Catal

      Volume: 353 Issue: 8 Pages: 1229-1233

    • DOI

      10.1002/adsc.201000944

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Biaryl Compounds Using Tandem Ruthenium-Catalyzed Ring-Closing Metathesis Chem2011

    • Author(s)
      Kazuhiro Yoshida, Hiroaki Shida, Hidetoshi Takahashi, and Akira Yanagisawa
    • Journal Title

      Eur. J

      Volume: 17 Issue: 1 Pages: 344-349

    • DOI

      10.1002/chem.201002074

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Carbocyclic Ring of Indoles Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis2011

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 4762-4765

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Biaryl Compounds Using Tandem Ruthenium-Catalyzed Ring-Closing Metathesis2011

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      Chem.Eur.J.

      Volume: 17 Pages: 344-349

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis of 4-Vinylindoles Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis2012

    • Author(s)
      Kazushi Hayashi, Kazuhiro Yoshida, and Akira Yanagisawa
    • Organizer
      12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto
    • Year and Date
      2012-11-15
    • Related Report
      2012 Final Research Report
  • [Presentation] 閉環エンインメタセシスを利用する置換ナフタレンおよび置換2-ナフトールの合成2012

    • Author(s)
      鹿野勇斗
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      東京、慶應義塾大学日吉キャンパス
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] ルテニウム触媒閉環エンインメタセシスを用いるインドールの合成2012

    • Author(s)
      林和史
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      東京、慶應義塾大学日吉キャンパス
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] Ring Size-Selective Ring-Closing Olefin Metathesis : Taking Advantage of the Deleterious Effect of Ethylene Gas2011

    • Author(s)
      鹿野勇斗
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋、名古屋大学東山キャンパス
    • Year and Date
      2011-09-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] 環サイズ選択的閉環オレフィンメタセシス:エチレンガスによる阻害効果の利用2011

    • Author(s)
      鹿野勇斗
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] ルテニウム触媒閉環メタセシスを用いるインドールおよびベンゾチオフェンの合成2011

    • Author(s)
      林和史
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] Synthesis of Heterocyclic Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Metathesis2010

    • Author(s)
      林和史
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2010-09-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] メタセシス反応とヨウ素試剤を利用する芳香族化合物の合成

    • Author(s)
      西井 佳奈
    • Organizer
      第15回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉、千葉大学西千葉キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] Enantioselective Synthesis of Greg Fu’s Planar-Chiral Fc*-DMAPs

    • Author(s)
      Masamichi Ogasawara
    • Organizer
      12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都、京都リーガロイヤルホテル
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis of 4-Vinylindoles Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis

    • Author(s)
      Kazushi Hayashi
    • Organizer
      12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都、京都リーガロイヤルホテル
    • Related Report
      2012 Annual Research Report
  • [Presentation] 閉環メタセシス反応を鍵反応とする面不斉 Ferroco-DMAP のエナンチオ選択的合成法の開発

    • Author(s)
      小笠原 正道
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 閉環エンインメタセシスと増炭反応を鍵反応として利用する芳香族化合物の合成

    • Author(s)
      西井 佳奈
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀、立命館大学びわこくさつキャンパス
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://ceres.s.chiba-u.ac.jp/

    • Related Report
      2012 Final Research Report
  • [Remarks] 研究室ホームページ

    • URL

      http://ceres.s.chiba-u.ac.jp/

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://ceres.s.chiba-u.ac.jp/

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://ceres.s.chiba-u.ac.jp/

    • Related Report
      2010 Annual Research Report
  • [Patent(Industrial Property Rights)] ビアリール化合物を製造する方法2010

    • Inventor(s)
      吉田和弘、高橋英寿、柳澤章
    • Industrial Property Rights Holder
      国立大学法人千葉大学
    • Patent Publication Number
      2010-208977
    • Filing Date
      2010-09-24
    • Related Report
      2012 Final Research Report

URL: 

Published: 2010-08-23   Modified: 2019-07-29  

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